Sr. Program Manager - Enablement Portfolio

We're looking for a

Sr. Program Manager - Enablement Portfolio

This role is Hybrid, Costa Rica

Sr. Program Manager - Enablement Portfolio

Position Summary
Sr. Program Manager - Enablement Portfolio leads the planning, coordination, governance, and reporting of Cornerstone University's strategic initiative portfolio. This role partners with leaders across the organization to drive execution, provide visibility into portfolio performance, support executive business reviews, and ensure strategic initiatives remain aligned with organizational priorities and business goals.

Key Responsibilities
• Lead the portfolio of strategic initiatives across Cornerstone University, ensuring alignment with business priorities and organizational goals.
• Partner with leaders across the organization to plan, prioritize, and coordinate strategic initiatives.
• Develop and maintain portfolio plans, project timelines, milestones, executive dashboards, and status reports.
• Monitor portfolio health and provide regular reporting on progress toward strategic goals, milestones, and business outcomes.
• Prepare materials, reporting, and insights for executive business reviews, governance meetings, and operational planning sessions.
• Analyze portfolio performance to identify trends, risks, dependencies, and opportunities, and provide recommendations to leadership.
• Support business reviews by providing visibility into initiative progress, organizational capacity, resource utilization, and overall portfolio performance.
• Facilitate governance meetings, document key decisions, track action items, and ensure follow-through on commitments.
• Support prioritization, capacity planning, and resource allocation across strategic initiatives.
• Establish and improve portfolio management standards, governance processes, and operational best practices.
• Partner with leadership to improve execution, accountability, and cross-functional collaboration.
• Perform other duties and special projects as assigned.

Qualifications
• Bachelor's degree or equivalent experience.
• 5+ years of experience in program management, portfolio management, business operations, strategy, or a related field.
• Experience leading complex cross-functional initiatives and managing multiple concurrent projects.
• Strong organizational, communication, analytical, and stakeholder management skills.
• Experience preparing executive-level reporting and business reviews.
• Proficiency with Microsoft Office and project management tools.
• Ability to influence without direct authority and build strong working relationships across all levels of the organization.

Our Growing Presence in Costa Rica

Cornerstone is excited to be building a new hub in Costa Rica as part of our continued investment in growing our global talent and capabilities. We are bringing together teams across a variety of functions, creating exciting opportunities for people to join us at the ground floor of this new chapter and help shape how we grow in the region.

We have invested in a new office in Costa Rica, with construction beginning soon, and we expect our presence and capabilities in the region to continue expanding over time. For those joining us now, this is a unique opportunity to help build something from the beginning, work alongside talented colleagues across Cornerstone globally, and be part of our longer-term growth in Costa Rica.

Employment Structure

As we establish our operations in Costa Rica and complete the process to operate under the country’s Free Trade Zone Regime, Cornerstone is partnering with Recluta, our local Employer of Record (EOR).

Our Culture

Spark Greatness. Shatter Boundaries. Share Success. Are you ready? Because here, right now – is where the future of work is happening. Where curious disruptors and change innovators like you are helping communities and customers enable everyone – anywhere – to learn, grow and advance. To be better tomorrow than they are today.

Who We Are:

At Cornerstone, we believe in AI that works in the service of people, amplifying their judgment to drive high-performing, future-ready organizations forward. Cornerstone Workforce AI™, the intelligence platform for workforce readiness, brings together workforce and labor market data into a proprietary Cornerstone People Graph™, translating signals into intelligence, targeting learning where it matters, developing critical skills, and surfacing hidden talent. Delivered as an open, enterprise platform across whatever application your people work in every day, Cornerstone Workforce AI is built for scale, security, and trust, with certified AI guardrails. As an industry leader, Cornerstone is helping approximately 7,000 organizations, 140M+ users, across 186 countries build continuous workforce readiness.

Check us out on LinkedIn, Comparably, Glassdoor, and Facebook!